Acylation Flashcards

(18 cards)

1
Q

What are acid anhydrides formed from?

A

Two carboxylic acids

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2
Q

Conditions, name and reagent of acylation reactions

A

Name: Nucleophilic Addition - Elimination

Condition: Gently heated

Reagent: Nucleophiles

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3
Q

Acid anhydride + water ->

A

Carboxylic acid + carboxylic acids

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4
Q

Acid anhydride + alcohol ->

A

Ester + Carboxylic acid

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5
Q

Acid anhydride + ammonia ->

A

Primary amide + carboxylic acid

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6
Q

Acid anhydride + primary amide ->

A

Secondary amide + carboxylic acid

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7
Q

Evidence HCl is produced

A

Steamy, white fumes

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8
Q

Acyl chloride + water ->

A

Carboxylic acid + HCl

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9
Q

Acyl chloride + alcohol ->

A

Ester + HCl

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10
Q

Acyl chlorde + ammonia ->

A

Amide + Ammonium chloride

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11
Q

Condition and observation between acyl chloride + ammonia

A

Ammonia in excess

White smoke from ammonium chloride

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12
Q

Acyl chloride + primary amide ->

A

Secondary amide + alkylammonium chloride salt

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13
Q

Conditions between acyl chloride + primary amide

A

Excess primary amide

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14
Q

Why are nucleophiles attracted to acyl chlorides in nucleophilic addition-elimination reactions

A

The delta positive charge on the C of the C=O bond

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15
Q

Mechanism of addition-elimination reactions

A

Nucleophile attacks C in the C=O bond.

C=O bond breaks with bonding pair of electrons and transfer to the O.

C-O bond reforms as C-Cl bond breaks.

N-H bond breaks.

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16
Q

What are the multiple industrial advantages of ethanoic anhydride over ethanoyl chloride?

A

Less reactive so safer to handle and store.

Cheaper.

Does not produce toxic HCl fumes.

Can be used in aspirin synthesis.

17
Q

What to react to produce aspirin

A

Ethanoic anhydride + 2-hydroxybenzoic acid

18
Q

What is the other substrate formed alongside aspirin